Macrocycles rapidly produced by multiple multicomponent reactions including bifunctional building blocks (MiBs)

Molecular Diversity

Volumn 9, Issue 1-3, 2005, Pages 159-169

  Wessjohann, Ludger A ^a   Ruijter, Eelco ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

Diversity oriented synthesis; Macrocycles; Multicomponent reactions; Natural products; Ugi reaction

Indexed keywords

ALKALOID DERIVATIVE; CYCLOPEPTIDE; FUNCTIONAL GROUP; MACROCYCLIC COMPOUND; NATURAL PRODUCT; VANCOMYCIN;

AMINO TERMINAL SEQUENCE; ATOM; BIOLOGY; CARBOXY TERMINAL SEQUENCE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; COMPLEX FORMATION; CONFORMATION; CRYSTALLIZATION; CYCLIZATION; DILUTION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; OLIGOMERIZATION; PRECURSOR; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; RING CLOSING METATHESIS; SEQUENCE ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

BIOLOGICAL FACTORS; CHEMISTRY, ORGANIC; DRUG DESIGN; HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 15444378113     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-005-1313-y     Document Type: Review

References (46)

1. Newman, D.J., Cragg, G.M. and Snader, K.M., Natural products as sources of new drugs over the period 1981-2002, J. Nat. Prod., 66 (2003) 1022-1037.
2. Henkel, T., Brunne, R.M., Mueller, H. and Reichel, F., Statistical investigation into the structural complementarity of natural products and synthetic compounds, Angew. Chem., 111 (1999) 688-691.
3. Rouhi, A.M., Rediscovering natural products, Chem. Eng. (2003) 77-107.
4. Lee, M.-L. and Schneider, G., Scaffold architecture and pharmacophoric properties of natural products and trade drugs: Application in the design of natural product-based combinatorial libraries, J. Comb. Chem., 3 (2001) 284-289.
5. Fehler, M. and Schmidt, J.M., Property distributions: Differences between drugs, natural products, and molecules from combinatorial chemistry, J. Chem. Inf. Comput. Sci., 43 (2003) 218-227.
6. Wessjohann, L.A. and Ruijter, E., Total and diversity-oriented synthesis of natural product(-like) macrocycles, Top. Curr. Chem., 243 in press.
7. Frobel, K., Naturstoffe - wie geht es weiter? In 12, Irseer Naturstofftage der DECHEMA e.V., 2000, Irsee.
8. Wessjohann, L.A., Ruijter, E., Garcia-Rivera, D. and Brandt, W., What can a chemist learn from nature's macrocycles? - a brief, conceptual view, Mol. Div. (2004) this issue.
9. Nubbemeyer, U., Synthesis of medium-sized lactams, Top. Curr. Chem., 216 (2001) 125-196.
10. Jin, Z., Muscarine, imidazole, oxazole and thiazole alkaloids, Nat. Prod. Rep., 20 (2003) 584-605.
11. Janvier, P., Bois-Choussy, M., Bienaymé, H. and Zhu, J., A one-pot four-component (ABC2) synthesis of macrocycles, Angew. Chem., 115 (2003) 835-838.
12. Schültingkemper, H., In Wessjohann, L. (ed.) The Combinatorial Diastereoselective Synthesis of Highly Functionalized Tetrahydropyrans, Master Thesis, IPB Halle, Germany and Hogeschool Enschede, The Netherlands, 2001; Ruijter, E., Schültingkemper, H. and Wessjohann, L.A., Highly substituted tetrahydropyrones from Hetero-Diels-Alder reactions of enals with stereochemical induction from chiral dienes, J. Org. Chem. (in press).
13. Schültingkemper, H., In Wessjohann, L. (ed.) The Combinatorial Diastereoselective Synthesis of Highly Functionalized Tetrahydropyrans, Master Thesis, IPB Halle, Germany and Hogeschool Enschede, The Netherlands, 2001; Ruijter, E., Schültingkemper, H. and Wessjohann, L.A., Highly substituted tetrahydropyrones from Hetero-Diels-Alder reactions of enals with stereochemical induction from chiral dienes, J. Org. Chem. (in press).
14. Lambert, J., Mitchell, J.P. and Roberts, K.D., The synthesis of cyclic peptides, J Chem. Soc. Perkin Trans., 1 (2001) 471-484.
15. Bordusa, F., Enzymes for peptide cyclization, Chembiochem, 2 (2001) 405-409.
16. Wessjohann, L.A., Synthesis of natural product-based compound libraries, Curr. Opin. Chem. Biol., 4 (2000) 303-309.
17. Nielsen, J., Combinatorial synthesis of natural products, Curr. Opin. Chem. Biol., 6 (2003) 297-305.
18. Dömling, A. and Ugi, I., Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed., 39 (2000) 3168-3210.
19. Failli, A., Immer, H. and Götz, M., The synthesis of cyclic peptides by the four component condensation (4CC), Can. J. Chem., 57 (1979) 3257-3261.
20. Bauer, S.M. and Armstrong, R.W., Total synthesis of motuporin (Nodularin-V), J. Am. Chem. Soc., 121 (1999) 6355-6366.
21. Schmidt, U. and Weinbrenner, S., The synthesis of eurystatin A, J. Chem. Soc. Chem. Commun. (1994) 1003-1004.
22. Owens, T.D., Araldi, G.-L., Nutt, R.F. and Semple, J.E., Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction-deprotection-acyl migration strategy, Tetrahedron Lett., 42 (2001) 6271-6274.
23. Beck, B., Larbig, G., Magnin-Lachaux, M., Picard, A., Herdtweck, E. and Dömling, A., Short and diverse route toward natural product-like macrocycles, Org. Lett., 5 (2003) 1047-1050.
24. Lee, D., Sello, J.K. and Schreiber, S.L., Pairwise use of complexity-generating reactions in diversity-oriented organic synthesis, Org. Lett., 2 (2000) 709-712.
25. Hebach, C. and Kazmaier, U., Via Ugi reactions to conformationally fixed cyclic peptides, Chem. Commun. (2003) 596-597.
26. Flanagan, D.M. and Joullie, M.M., Studies directed toward the total synthesis of 14-membered cyclopeptide alkaloids: Synthesis of a linear precursor to nummularine-F, Synth. Commun., 20 (1990) 459-467.
27. Bowers, M.M., Carroll, P. and Joullie, M.M., Model studies directed toward the total synthesis of 14-membered cyclopeptide alkaloids: Synthesis of prolyl peptides via a four-component condensation, J. Chem. Soc. Perkin Trans., 1 (1989) 857-865.
28. NAr-based cycloetherification, Org. Lett., 3 (2001) 4079-4082.
29. Cristau, P., Vors, J.-P. and Zhu, J., Solid-phase synthesis of natural product-like macrocycles by a sequence of Ugi-4CR and SNAr-based cycloetherification, Tetrahedron Lett., 44 (2003) 5575-5578.
30. Lobrégat, V., Alcaraz, G., Bienaymé, H. and Vaultier, M., Application of 'resin-capture-release' methodology to macrocyclisation via intramolecular Suzuki-Miyaura coupling, Chem. Commun. (2001) 817-818.
31. Orru, R.V.A., de Greef, M., Abeln, S., Belkasmi, K., Dömling, A. and Wessjohann, L.A., A short and flexible route to cyclopeptide alkaloids, In The 12th European Symposium on Organic Chemistry (ESOC 12), 2001, O-36, Groningen, The Netherlands.
32. Weber, L., Multi-component reactions and evolutionary, chemistry, Drug Disc. Today, 7 (2002) 143-147.
33. Weber, L., The application of multi-component reactions in drug discovery, Curr. Med. Chem., 9 (2002) 1241-1253.
34. Gámez-Montaño, R., González-Zamora, E., Potier, P. and Zhu, J., Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure, Tetrahedron, 58 (2002) 6351-6358.
35. Second International Conference on Multi Component Reactions, Combinatorial and Related Chemistry, 2003, Genova.
36. Otto, S., Furlan, R.L.E. and Sanders, J.K.M., Recent developments in dynamic combinatorial chemistry, Curr. Opin. Chem. Biol., 6 (2003) 321-327.
37. Gournelis, D.C., Laskaris, G.G. and Verpoorte, R., Cyclopeptide alkaloids, Nat. Prod. Rep., 14 (1997) 75-82.
38. Laib, T. and Zhu, J., An asymmetric total synthesis of sanjoinine G1, Tetrahedron Lett., 40 (1999) 83-86.
39. Temal-Laib, T., Chastanet, J. and Zhu, J., A convergent approach to cyclopeptide alkaloids: Total synthesis of sanjoinine G1, J. Am. Chem. Soc., 124 (2002) 583-590.
40. Lee, S.-S., Su, W.-C. and Liu, K.C.S.C., Cyclopeptide alkaloids from stems of paliurus ramosissimus, Phytochemistry, 58 (2001) 1271-1276.
41. Boisnard, S. and Zhu, J., Studies toward the total synthesis of RP-66453, Tetrahedron Lett., 43 (2002) 2577-2580.
42. Venkatraman, S., Njoroge, F.G. and Girijavallabhan, V., Application of ruthenium induced cyclization for construction of strained biaryl ether macrocyclic compounds, Tetrahedron Lett., 58 (2002) 5453-5458.
43. NAr reaction, Tetrahedron Lett., 42 (2001) 8765-8768.
44. NAr reaction: Problems and solutions using arylserine-Ru complexes, Tetrahedron Lett., 41 (2000) 5991-5996.
45. Pearson, A.J. and Bignan, G., Studies on the applications of arene-ruthenium complexes in synthetic approaches to vancomycin: A mild procedure for the formation of chlorinated aryl ethers and triaral ethers, Tetrahedron Lett., 37 (1996) 735-738.
46. Abeln, S. In Wessjohann, L.A. and van der Baan, J. (Eds.) Cyclopeptide Alkaloids: A Novel Synthesis Using the Multi Component Ugi Reaction, Master Thesis, Vrije Universiteit Amsterdam, The Netherlands, 2000.